CN109593095B - X-type hetero-condensed perylene aromatic hydrocarbon double-spiro-alkene functional molecular material and preparation and application thereof - Google Patents
X-type hetero-condensed perylene aromatic hydrocarbon double-spiro-alkene functional molecular material and preparation and application thereof Download PDFInfo
- Publication number
- CN109593095B CN109593095B CN201811534670.6A CN201811534670A CN109593095B CN 109593095 B CN109593095 B CN 109593095B CN 201811534670 A CN201811534670 A CN 201811534670A CN 109593095 B CN109593095 B CN 109593095B
- Authority
- CN
- China
- Prior art keywords
- formula
- spiro
- aromatic hydrocarbon
- molecular material
- hetero
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
Abstract
The invention belongs to the field of photoelectric materials, and particularly discloses a X-type double-spiro-alkene functional molecular material of hetero-condensed perylene aromatic hydrocarbon. The invention also discloses a preparation method and an application method of the X-type double-spiro-alkene functional molecular material of the hetero-fused perylene aromatic hydrocarbon. The perylene and the conjugate system are fused in a three-dimensional space, the double-spiro-alkene functional molecule of X-type hetero-fused perylene aromatic hydrocarbon is constructed in a hetero-thickening mode, and the pi-electron conjugate structure and the physical properties of the conjugate molecule are regulated and controlled, so that the multi-functional integrated organic molecular material with solid fluorescence, charge transmission, chiral light absorption and chiral circular polarization luminescence is formed. Can be applied to electronic devices, chiral optical elements and the like which are required by multifunctional materials.
Description
Technical Field
The invention relates to the field of functional molecular materials, in particular to a photoelectric molecular material
Background
The multifunctional organic material is a kind of organic small molecule, supermolecule and high molecule material with unique physical and chemical properties, and it contains extensive and artificial material with development prospect. Since the seventies of the last century, research on multifunctional photoelectric materials based on organic molecules has attracted much attention, and the multifunctional photoelectric materials have become a hot point of research in the fields of chemistry, material science and the like. The Polycyclic Aromatic Hydrocarbon System (PAHs) can be used as an organic multifunctional material with unique photoelectric properties due to the pi-conjugated skeleton, rigid planar structure and strong intermolecular pi-pi interaction, and has application value in organic photoelectronic elements. Among many conjugated molecular materials, polycyclic aromatic hydrocarbons represented by perylene derivatives (also called perylene derivatives) have been developed as functional derivatives with unique photoelectric activity due to their wide performance regulation space. However, the poor solubility, poor chemical stereoselectivity and narrow regioselectivity of perylene lead to the difficulty in the functionalized modification of perylene core matrix, and greatly limit the improvement of the material properties. At present, research on perylene derivatives with Perylene Diimide (PDI) as the leading factor solves some of the above problems. With the advance of modern organic synthesis technology, pi extension of perylene systems in a Diagonally diagonal (formula a) manner is made possible. Through alkylation or alkoxylation modification at bay, the pi system can extend in three-dimensional space and has axial chirality, and the three-dimensional molecule is favorable for improving molecule solubility and aggregate luminescence, and is convenient for preparing functional molecular devices by a solvent method. More importantly, the problem that the traditional three-dimensional system is difficult to realize carrier transmission is solved through the introduction of heteroatoms. Thus, chemical modification of the pi system provides a single molecule with integrated multifunctional properties.
Disclosure of Invention
In order to solve the technical defects that the optical performance and the transmission performance cannot be combined due to the existence of light quenching in the conventional perylene compounds, the invention provides a double-spiro functional molecule of X-type hetero-condensed perylene aromatic hydrocarbon, and aims to construct a novel multifunctional molecular material.
The second purpose of the invention is to provide a preparation method of the X-type hetero-fused perylene double-spiro-alkene functional molecule of aromatic hydrocarbon and the integrated multifunctional photoelectric property thereof, and the functional molecule can be successfully prepared by the perylene parent nucleus chemical modification mechanism.
The third purpose of the invention is to provide the application of the X-type hetero-fused perylene double-spiro-alkene functional molecular material in photoelectric functional molecular materials.
The X-type double-spiro functional molecular material of the hetero-fused perylene aromatic hydrocarbon is characterized by having a structural general formula of a formula 1:
in the formula 1, R is1、R2、R3、R4Independently selected from-Cl, -Br, -I, -CN, C1-C24 alkyl, C3-C24 cycloalkyl, C1-C24 alkoxy, halogenated C1-C24 alkyl, halogenated C3-C24 cycloalkyl or halogenated C1-C24 alkoxy, and aryl;
X1、X2、X3、X4independently selected from S, Se, O and N;
Ar1、Ar2、Ar3、Ar4independently is five-membered heterocyclic aryl, phenyl, substituted phenyl, six-membered heterocyclic aryl or condensed ring aryl.
The compound with the structural formula is a conjugated epitaxial three-dimensional perylene derivative; the characteristics of integrating photoelectric multiple functions into a whole are researched. The compound is a three-dimensional conjugated system, and can be used for preparing samples by a dissolution method; and the compounds have integrated solid state fluorescence and charge transport, as well as configuration retention and chiral optical properties.
The invention provides perylene derivatives extending in an oblique diagonal (Diagnonely) Pi mode for the first time, and particularly provides three-dimensional X-type double-spiro functional molecules formed by perylene, benzothiophene and the like, so that regular J-type and H-type staggered stacking modes can be realized in small molecules, and organic functional molecules integrating solid fluorescence, charge transmission, chiral light absorption and chiral polarized fluorescence emission can be realized. The regulation and control of material performance on a molecular level provides a wider development space for electronic devices and optical elements required by high-end materials and application thereof.
Preferably, in formula 1, R1、R2、R3、R4Independently C1-24 alkyl, C1-24 alkoxy or aryl.
More preferably, in formula 1, R1、R2、R3、R4Independently C1-4 alkoxy.
Even more preferably, R is1、R2、R3、R4Are selected from the same group.
Most preferably, said R1、R2、R3、R4Are all-OC4H9(ii) a N-butoxy is preferred.
In the formula 1, X1-X4 are S, Se, O and N independently;
preferably, X1-X4 are selected from the same elements.
More preferably, all of X1 to X4 are S.
Ar1、Ar2、Ar3、Ar4Is a fused group at peri-position of perylene ring, and can form a double-spiro functional molecule of X-type hetero fused perylene arene in space through the combination of the aryl. The aromatic group can be five-membered heterocyclic aryl, phenyl, substituted phenyl, six-membered heterocyclic aryl and substituted six-membered heterocyclic aryl; an aromatic hydrocarbon group in which any two or more aromatic rings are condensed in a five-or six-membered aromatic group.
Preferably, Ar is1、Ar2、Ar3、Ar4Are selected from the same group; further preferred is a phenyl group, a substituted phenyl group or a five-membered heterocyclic aryl group.
Preferably, the X-type double-spiro-alkene functional molecular material of the hetero-fused perylene aromatic hydrocarbon has a structural formula of 1-A:
still more preferably, the X-type double-spiro-alkene functional molecular material of the hetero-fused perylene aromatic hydrocarbon has a structural formula of 1-A-1:
the absorption spectrum of the double-spiro-alkene functional molecular material of the X-type hetero-fused perylene aromatic hydrocarbon covers the ultraviolet spectral region and the visible spectral region of 250-500 nm.
Preferably, it has solid fluorescent properties, phi thereoff57% chiral optical resolution, chiral light emission glum＝1.09×10-3；
Further preferably, it has a P-type semiconductorTypical characteristics of the body, its transmission efficiency is 0.02cm2V-1s-1-0.1cm2V-1s-1。
The invention discloses a preparation method and multifunctional property of a double-spiro-alkene functional molecular material of X-type hetero-fused perylene aromatic hydrocarbon, wherein the compound shown in the formula 2 is cyclized and coupled to obtain:
in the formula 1, R is1、R2、R3、R4Independently selected from-Cl, -Br, -I, -CN, C1-C24 alkyl, C3-C24 cycloalkyl, C1-C24 alkoxy, halogenated C1-C24 alkyl, halogenated C3-C24 cycloalkyl or halogenated C1-C24 alkoxy, aryl
X1、X2、X3、X4Independently selected from S, Se, O and N;
Ar1、Ar2、Ar3、Ar4independently is five-membered heterocyclic aryl, phenyl, substituted phenyl, six-membered heterocyclic aryl or condensed ring aryl.
The selection and the preferable range of each substituent of the formula 2 are equivalent to those of the formula 1.
Preferably, the additive is propylene oxide
Preferably, the molar ratio of the compound of formula 2 to the oxidant is 1: 4-8.
Preferably, the temperature of the cyclization coupling reaction is 50-70 ℃, and more preferably 55 ℃.
According to the preparation method, the compound shown in the formula 2 is obtained by coupling the compound shown in the formula 3 and the compound shown in the formula 4;
in formula 3, X is halogen, preferably-Br or-I;
in the formula 4, A is a coupling leaving group; y is X1、X2、X3Or X4；
Ar is Ar1、Ar2、Ar3Or Ar4；Ar1、Ar2、Ar3、Ar4Preferably the same group.
In the formulae 3 and 4, the selection ranges of the substituents are the same as those in the formula 1.
Preferably, the coupling is a Suzuki coupling reaction.
Preferably, X is-Br.
Preferably, A is-B (OH)2。
The molar ratio of the compound shown in the formula 3 to the compound shown in the formula 4 is 1: 1-3.
The Suzuki coupling reaction is carried out under the catalysis of a palladium catalyst, and the preferred catalyst is Pd (dppf) Cl2。
The temperature of the Suzuki coupling reaction is 80-90 ℃; preferably 85 deg.c.
The invention discloses a preparation method of an optimized X-type hetero-fused perylene aromatic double-spiro-ene functional molecular material, which comprises the following steps:
step (1): reacting a compound shown as a formula 3-A and a compound shown as a formula 4-A in the presence of a catalyst to obtain a compound shown as a formula 2-A;
step (2): reacting the compound shown in the formula 2-A with an oxidant to prepare the X-type hetero-fused perylene aromatic double-spiro-alkene functional molecular material shown in the formula 1;
preferably, in the step (1), the compound of formula 3-A and 1-3 eqv formula 4-A, 0.2eqv catalyst are subjected to Suzuki coupling reaction.
In the step (1), the reaction is carried out in a protective atmosphere; the preferred reaction solvent is dioxane at 5:1 and water.
Preferably, the reaction temperature is 85 ℃; the catalyst is Pd (dppf) Cl2；
After the reaction in the step (1), extracting with dichloromethane and water, taking an organic layer, and removing the solvent to obtain a formula 2-A;
in the step (2), the molar ratio of the compound shown in the formula 2-A to the oxidant is 1: 4-8.
In the step (2), the reaction temperature is preferably room temperature; the reaction solvent is preferably 9:5:1 trichloromethane, acetic acid and propylene oxide;
preferably, the additive is propylene oxide.
The preferred preparation method of the invention has the synthesis circuit shown in the formula 1:
the invention provides an application of the X-type hetero-fused perylene aromatic double-spiro-alkene functional molecular material, and the conjugated functional molecule is applied to the fields of organic photoelectric materials, multifunctional devices, functional materials and the like.
Further preferably, the three-dimensional conjugated molecular material is used for preparing organic field effect transistors, organic light emitting diodes, chiral optical elements, polarized light emitting organic field effect transistors and the like.
Advantageous effects
The X-type double-spiro-alkene functional molecular material of the hetero-fused perylene aromatic hydrocarbon is mainly characterized in that the integrated regulation and control of a three-dimensional structure and photoelectric properties thereof are realized through the chemical modification of perylene. Successfully introduces solvent groups such as alkyl and the like to construct an organic material which can be easily operated by a solvent method. .
Perylene precursors are susceptible to photo-quenching during molecular aggregation, which makes both fluorescence and charge transport properties incompatible. The spiro compound has chiral optical activity due to the structural characteristics of distorted conjugation, but effective packing between molecules is difficult to realize. The functional molecule with the X-type function in the spatial configuration formed by combining the perylene and the spiro is innovatively provided, the double-spiro functional molecule of the X-type hetero-fused perylene aromatic hydrocarbon is constructed in a hetero-thickening mode, the conjugated structure and the physical properties of the conjugated molecule are regulated, and the J-type and H-type staggered stacking mode is realized, so that the functional molecule becomes a multifunctional integrated material of solid fluorescence, charge transmission, chiral light absorption and chiral polarized fluorescence, and can be applied to electronic devices, optical elements and the like which are oriented to the requirements of high-end materials.
Drawings
FIG. 1 is a NMR spectrum of a compound of formula 1-A-1 obtained in example 1.
FIG. 2 is a nuclear magnetic resonance carbon spectrum of formula 1-A-1 obtained in example 1.
FIG. 3 is a mass spectrum of formula 1-A-1 obtained in example 1.
FIG. 4 is a UV-visible spectrum of formula 1-A-1 prepared in example 1.
FIG. 5 is a diffraction structural diagram of a single crystal of formula 1-A-1 obtained in example 1.
FIG. 6 is a fluorescence plot of formula 1-A-1 prepared in example 1;
FIG. 7 is a graph of the mobility of formula 1-A-1 prepared in example 1;
FIG. 8 is a graph showing chiral optical absorption, circular polarized light emission and theoretical calculation of pure enantiomer of formula 1-A-1 prepared in example 1.
Detailed Description
Example 1
Synthesis of formula 1-A-1:
adding Per-4Br (in formula 3-A, R1-R4 are all n-butoxy groups) into dioxane, adding 2-methylthio phenylboronic acid (1.2 equivalent), Pd (dppf) Cl and inert gas2(0.02 eq.) and a reaction solvent (a mixed solvent of dioxane and water in a volume ratio of 5: 1) at 85 ℃ (± 5 ℃) to perform suzuki reaction, monitoring the reaction by thin layer chromatography, and purifying the residue by silica gel chromatography or recrystallization to obtain the intermediate product of equation 1.
Adding the obtained product, chloroform, acetic acid and propylene oxide into an eggplant-shaped bottle, cooling to zero centigrade, slowly adding an iodine solution (10 equivalents) dropwise, heating the reactant to 55 ℃ (± 5 ℃) for reacting for a plurality of hours, monitoring the reaction by using a thin layer chromatography, quenching the reaction by using sodium bicarbonate after the reaction, and performing aftertreatment to obtain a crystal purified sample to obtain the formula 1-A-1 (the yield is 89%, and the purity is more than 99.9%).
The structure of the compound of the formula 1-A-1 is confirmed by means of nuclear magnetic resonance hydrogen spectrum, carbon spectrum, mass spectrum, ultraviolet-visible spectrum, single crystal diffraction and the like.
1H NMR(400MHz,CDCl3):δ9.14(d,J＝7.8Hz,4H),8.16(d,J＝7.6Hz,4H),7.65-7.57(m,8H),3.78-3.73(m,4H),3.48-3.42(m,4H),1.71-1.56(m,8H),1.23-1.13(m,8H),0.53(t,J＝7.2Hz,12H)。
13C NMR(100MHz,CDCl3):δ154.91,139.24,135.63,135.59,134.01,127.36,126.22,125.59,124.93,122.27,116.27,115.37,32.51,19.20,13.54。
HRMS(MALDI-TOF,m/z)calcd for C60H52O4S4[M]+,964.2748；found:964.2724(error＝-2.49ppm)。
The solid fluorescence quantum yield of the compound with the structural formula is 57% (see figure 6), and the hole mobility is 0.02cm2V-1s-1See fig. 7), and a circularly polarized fluorescence factor glumIs 1.09X 10-3The chiral optical resolution is shown in figure 8.
Example 2 Synthesis of formula 1-A-2
The chemical synthesis method is shown in design formula 2:
compared with example 1, the only difference is that 2-methylselenophenylboronic acid is used to replace 2-methylthiophenylboronic acid in example 1; other operation steps and parameter control are the same. The product yield is 85% and the chromatographic purity is more than 99.9%.
Example 3 Synthesis of formula 1-A-3
The synthesis equation is shown in equation 3:
compared with example 1, the difference is only that the raw material of the present case is used to replace the 1-methylthio-2-naphthalene boronic acid of example 1; other operation steps and parameter control are the same. The product yield is 83 percent, and the purity is more than 99.9 percent.
Claims (12)
- The X-type double-spiro functional molecular material of the hetero-fused perylene aromatic hydrocarbon is characterized by having a structural general formula of a formula 1:
in the formula 1, R is1、R2、R3、R4Independently selected from-Cl, -Br, -I, -CN, C1-C24 alkyl, C3-C24 cycloalkyl, C1-C24 alkoxy, halogenated C1-C24 alkyl, halogenated C3-C24 cycloalkyl or halogenated C1-C24 alkoxy;X1、X2、X3、X4independently selected from S, Se or O;Ar1、Ar2、Ar3、Ar4is phenyl. - 2. The double-spiro-ene functional molecular material of X-type hetero-fused perylene aromatic hydrocarbon according to claim 1, wherein in formula 1, R is1、R2、R3、R4Independently is C1-C24 alkyl or C1-C24 alkoxy.
- 3. The double-spiro-ene functional molecular material of X-type hetero-fused perylene aromatic hydrocarbon according to claim 1, wherein in formula 1, R is1、R2、R3、R4Independently C1-4 alkoxy.
- 4. The X-type heterofused perylene aromatic bis-spiro-ene functional molecular material of claim 1, wherein R is R1、R2、R3、R4Are selected from the same group.
- 5. The double-spiro-ene functional molecular material of X-type hetero-fused perylene aromatic hydrocarbon according to claim 1, wherein X is X1、X2、X3、X4Are selected from the same elements.
- 6. The bis of type X hetero-fused perylene arene of claim 1A spiroalkene functional molecular material, characterized in that X1、X2、X3、X4Is S.
- 7. The preparation method of the double-spiro-alkene functional molecule of the X-type hetero-fused perylene aromatic hydrocarbon as claimed in any one of claims 1 to 6, characterized in that the compound shown in the formula 2 is cyclized under the action of an additive and an oxidant to obtain: the additive is acetic acid and epoxy propane, and the oxidant is iodine;
formula 2In the formula 2, R is1、R2、R3、R4Independently selected from-Cl, -Br, -I, -CN, C1-C24 alkyl, C3-C24 cycloalkyl, C1-C24 alkoxy, halogenated C1-C24 alkyl, halogenated C3-C24 cycloalkyl or halogenated C1-C24 alkoxy;X1、X2、X3、X4independently selected from S, Se or O;Ar1、Ar2、Ar3、Ar4is phenyl. - 8. The method according to claim 7, wherein the temperature of the cyclization reaction is in the range of 50 to 70 ℃.
- 9. The method according to claim 7 or 8, wherein the compound of formula 2 is obtained by coupling a compound of formula 3 with a compound of formula 4;
formula 3
Formula 4In formula 3, X is halogen;in the formula 4, A is a coupling leaving group; y is X1、X2、X3Or X4(ii) a Ar is Ar1、Ar2、Ar3Or Ar4。 - 10. The method of claim 9, wherein the coupling is a Suzuki coupling;the X is-Br;a is-B (OH)2；The molar ratio of the compound shown in the formula 3 to the compound shown in the formula 4 is 1: 1-3;the Suzuki coupling reaction is carried out under the catalysis of palladium as a catalyst;the temperature of the Suzuki coupling reaction is 80-90 ℃.
- 11. The method of claim 10, wherein the catalyst is pd (dppf) Cl2。
- 12. The application of the double-spiro-alkene functional molecule of the X-type hetero-fused perylene aromatic hydrocarbon as claimed in any one of claims 1 to 6 is characterized in that the double-spiro-alkene functional molecule is used for luminescent materials and electronic materials.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811534670.6A CN109593095B (en) | 2018-12-14 | 2018-12-14 | X-type hetero-condensed perylene aromatic hydrocarbon double-spiro-alkene functional molecular material and preparation and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811534670.6A CN109593095B (en) | 2018-12-14 | 2018-12-14 | X-type hetero-condensed perylene aromatic hydrocarbon double-spiro-alkene functional molecular material and preparation and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109593095A CN109593095A (en) | 2019-04-09 |
| CN109593095B true CN109593095B (en) | 2020-05-08 |
Family
ID=65961923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811534670.6A Active CN109593095B (en) | 2018-12-14 | 2018-12-14 | X-type hetero-condensed perylene aromatic hydrocarbon double-spiro-alkene functional molecular material and preparation and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109593095B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111559973B (en) * | 2020-04-21 | 2021-09-21 | 中国科学院化学研究所 | Spiroalkene derivative and preparation method and application thereof |
| CN112778105B (en) * | 2020-12-31 | 2021-12-10 | 湖南大学 | Quadruple spiroalkene free radical molecule with thermally induced hysteresis loop and preparation method and application thereof |
| CN114957102B (en) * | 2022-05-16 | 2023-11-07 | 湖南大学深圳研究院 | Amide nitroxide free radical modified perylene molecule and preparation and application thereof |
| CN115141211A (en) * | 2022-06-22 | 2022-10-04 | 湖南大学深圳研究院 | Sulfur-embedded pentalene-fused perylene functional molecular material and preparation and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011068950A1 (en) * | 2009-12-03 | 2011-06-09 | The Trustees Of Columbia University In The City Of New York | Hierarchical assembly of nanostructured organic heterojunctions for photovoltaic devices |
| WO2017106852A1 (en) * | 2015-12-18 | 2017-06-22 | The Trustees Of Princeton University | Single-junction organic photovoltaic devices having high open-circuit voltages and applications thereof |
-
2018
- 2018-12-14 CN CN201811534670.6A patent/CN109593095B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011068950A1 (en) * | 2009-12-03 | 2011-06-09 | The Trustees Of Columbia University In The City Of New York | Hierarchical assembly of nanostructured organic heterojunctions for photovoltaic devices |
| WO2017106852A1 (en) * | 2015-12-18 | 2017-06-22 | The Trustees Of Princeton University | Single-junction organic photovoltaic devices having high open-circuit voltages and applications thereof |
Non-Patent Citations (3)
| Title |
|---|
| Hexathienocoronenes: Synthesis and Self-Organization;Long Chen,等;《Journal of the American Chemical Society》;20121015;第134卷(第43期);第17869− 17872页 * |
| Reticulated Heterojunctions for Photovoltaic Devices;Alon A. Gorodetsky，等;《Angew. Chem. Int. Ed.》;20100916;第49卷(第43期);第7909-7912页 * |
| Shape-shifting in contorted dibenzotetrathienocoronenes;Chien-Yang Chiu，等;《Chemical Science》;20110518(第2期);第1480-1486页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109593095A (en) | 2019-04-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109593095B (en) | X-type hetero-condensed perylene aromatic hydrocarbon double-spiro-alkene functional molecular material and preparation and application thereof | |
| Chen et al. | Tetraphenylpyrazine-based AIEgens: facile preparation and tunable light emission | |
| CN107089990B (en) | It is a kind of using fluorenes as the organic compound of core and its application on organic electroluminescence device | |
| CN107021926A (en) | A kind of compound containing azepine spiro fluorene and nitrogenous hexa-member heterocycle and its application on OLED | |
| CN107337680B (en) | It is a kind of using fluorenes as the organic compound of core and its application in OLED device | |
| CN109748909A (en) | The compound of a kind of fluorenes of xanthene containing spiral shell and nitrogenous hexa-member heterocycle, preparation method and its application in organic electroluminescence device | |
| CN108503657B (en) | Boron-nitrogen doped fused ring aromatic hydrocarbon containing five-membered heterocycle and synthetic method and application thereof | |
| Gu et al. | Understanding the structure-determining solid fluorescence of an azaacene derivative | |
| CN109096313B (en) | Preparation method of trimeric indenyl corrole-porphyrin-fullerene star-shaped compound | |
| CN107602542A (en) | A kind of organic compound containing dibenzo hexatomic ring and its application | |
| KR20200026162A (en) | Organic semiconducting material and its synthesis and organic semiconducting component with the material | |
| CN109575039A (en) | A kind of azines organic compound and its application | |
| CN108218853A (en) | It is a kind of using the nitrogenous hexa-member heterocycle of dibenzo as the compound of core and its application on organic electroluminescence device | |
| CN111138389B (en) | Dehydroabietic acid triarylamine D-pi-A type compound with furan derivative as pi bridge and synthesis method thereof | |
| CN110668975B (en) | Dehydroabietic acid triarylamine D-pi-A type compound with benzene derivative as pi bridge and synthesis method thereof | |
| Di et al. | Achieving high-performance narrowband blue MR-TADF emitters by suppressing isomer formation and extending π-conjugate skeletons | |
| CN109796449A (en) | It is a kind of using pyridine as the compound of core and its application on organic electroluminescence device | |
| CN110372679A (en) | It is a kind of using aryl ketones as the compound of core, preparation method and its application on OLED | |
| CN114621274B (en) | Boron nitride compound, organic electroluminescent composition and organic electroluminescent device comprising same | |
| CN116547255A (en) | Methods, reaction compositions, deuterated anthracene compounds, and compositions for preparing deuterated anthracene compounds | |
| CN111808097B (en) | Solvent yellow 184 derivative and preparation method and application thereof | |
| CN116507598A (en) | Methods, reaction compositions, deuterated anthracene compounds, and compositions for preparing deuterated anthracene compounds | |
| CN110642830B (en) | Dehydroabietic acid triarylamine D-pi-A type compound with thiophene derivative as pi bridge and synthesis method thereof | |
| CN113201022A (en) | Small conjugated phosphorescent metal iridium (III) complex with isomer and preparation method and application thereof | |
| Yagi et al. | Synthesis and light absorption/emission properties of novel bis-squaraine dyes with extensively conjugated π-electron systems |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |